Sodium Hydroxide → 2-{4-[6-chloro-2-[3-(4-pyridinyl)propyl]-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}ethanol

HRID 2077802Notes

Reaction equation

C([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[CH:19]=[C:18]([Cl:20])[C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[NH:25][C:26](=O)[CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)=[CH:9][CH:8]=1)(=O)C.[OH-].[Na+]>C(O)C>[Cl:20][C:18]1[C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]2[N:25]=[C:26]([CH2:27][CH2:28][CH2:29][C:30]3[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=3)[N:13]([C:10]3[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][OH:4])=[CH:8][CH:9]=3)[C:14]=2[CH:19]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 2-(4-{[5-chloro-2-{[4-(4-pyridinyl)butanoyl]amino}-4-(trifluoromethyl)phenyl]amino}phenyl)ethyl acetate (step 3, 220 mg, 0.42 mmol) and 2N NaOH (15 ml) in ethanol (20 ml) was stirred at 40° C. for 7 h. The solvent was removed and the residue was added water (50 ml). The mixture was extracted with ethyl acetate (100 ml). The organic layer was washed with brine (50 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with dichloromethane:methanol (20:1) to afford 105 mg (54%) of the title compound as pale brown oil.

Workup

customThe solvent was removed
additionthe residue was added water (50 ml)
extractionThe mixture was extracted with ethyl acetate (100 ml)
washThe organic layer was washed with brine (50 ml)
dry with materialdried (Na2SO4)
customAfter removal of solvent
customthe crude product was purified by flash column chromatography
washeluting with dichloromethane:methanol (20:1)

Sources & evidence

ORD record: ord-ac9f2a7edfaf4555922da2dcf473dad4
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928119B2

Reaction notes

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